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Further Information

Related Reactions
Tishchenko Reaction
Synthesis of aldehydes
Synthesis of ketones

Oppenauer Oxidation

The aluminium-catalyzed hydride shift from the α-carbon of an alcohol component to the carbonyl carbon of a second component, which proceeds over a six-membered transition state, is named Meerwein-Ponndorf-Verley-Reduction (MPV) or Oppenauer Oxidation (OPP) depending on the isolated product. If aldehydes or ketones are the desired products, the reaction is viewed as the Oppenauer Oxidation.

Non-enolizable ketones with a relatively low reduction potential, such as benzophenone, can serve as the carbonyl component used as the hydride acceptor in this oxidation.

Recent Literature

Oppenauer Oxidation of Secondary Alcohols with 1,1,1-Trifluoroacetone as Hydride Acceptor
R. Mello, J. Martínze-Ferrer, G. Asensio, M. E. González-Núñez, J. Org. Chem., 2007, 72, 9376-9378.

Efficient and Selective Al-Catalyzed Alcohol Oxidation via Oppenauer Chemistry
C. R. Graves, B.-S. Zeng, S. T. Nguyen, J. Am. Chem. Soc., 2006, 128, 12596-12597.

Practical Oppenauer (OPP) Oxidation of Alcohols with a Modified Aluminium Catalyst
T. Ooi, H. Otshuka, T. Miura, H. Ichikawa, K. Maruoka, Org. Lett., 2002, 4, 2669-2672.

Oxidation of Primary Alcohols and Aldehydes to Carboxylic Acids via Hydrogen Atom Transfer
W.-Y. Tan, Y. Lu, J.-F. Zhao, W. Chen, H. Zhang, Org. Lett., 2021, 23, 6648-6653.

Copper-Catalyzed Hydroalumination of Allenes with Diisobutylaluminum Hydride: Synthesis of Allylic Ketones with α-Quaternary Centers via Tandem Allylation/Oppenauer Oxidation
S. Lee, S. Lee, Y. Lee, Org. Lett., 2020, 22, 5806-5810.

General Transition Metal-Free Synthesis of NH-Pyrroles from Secondary Alcohols and 2-Aminoalcohols
J.-A. Shin, J. Kim, H. Lee, S. Ha, H.-Y. Lee, J. Org. Chem., 2019, 84, 4558-4565.